Compare Vacation Rentals & Airbnb in Oakville

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Oakville vacation rentals
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664 Rentals and Airbnb in Oakville

Best family friendly Oakville vacation rentals

Among the 664 accommodations in Oakville, here are the 4 best family friendly rentals

Luxury Retreat In Top Location - Oakville
9.6 63 reviews
Oakville
28/08 – 16/09
$158/nighttotal: $3002 (19 )

Luxury Retreat In Top Location

2 4
apartment , Milton
This excellent, family-friendly basement flat in a prestigious Milton neighbourhood is conveniently located near the GO station, Walmart, and Canadian Superstore.
The two-bedroom, one-bathroom self-catering apartment sleeps five, boasts a fully equipped kitchen including a dishwasher, high-speed Wi-Fi, Netflix, and parking, offering comfortable accommodation near Lakeshore and Milton town centre.
Stunning 4+1br Family Oasis @Oakville +Ev Charger - Oakville
10 17 reviews
Oakville
04/07 – 10/07
$470/nighttotal: $2820 (6 )

Stunning 4+1br Family Oasis @Oakville +Ev Charger

1 8
house , Milton
This five-bedroom, two-bathroom townhouse, offering accommodation for up to ten guests, is located near Dundas and Trafalgar in Oakville, a mere 15-kilometre drive from the Oakville waterfront and a significant halal food hub. Guests can enjoy ultra-fast internet, Rogers Ignite TV, full access to two floors and a backyard, with amenities including air conditioning, parking, and a kitchen, whilst being within walking distance of parks, Walmart, and various cafés.
2026 Fifa |40 Mins To Bmo Field |Oakville Go Train - Oakville
9.8 89 reviews
Oakville
23/06 – 25/06
$485/nighttotal: $970 (2 )

2026 Fifa |40 Mins To Bmo Field |Oakville Go Train

1 2
apartment , Toronto
This five-bedroom, three-bathroom house in Uptown Oakville offers self-catering for up to ten guests, conveniently located within 1.6km of Oakville Place shopping centre, 0.96km from Sheridan College, and 0.8km from a drive-in cinema.
The property features a fully equipped kitchen, a spacious living room with a 65" smart TV, two workspaces, a private enclosed garden, and family-friendly amenities including a high chair, children's books and toys; self check-in is available.
Cozy 2 Bedroom Basement Apart - Oakville
10 4 reviews
Oakville
01/08 – 30/09
$153/nighttotal: $9180 (60 )

Cozy 2 Bedroom Basement Apart

1 4
apartment , Toronto
This two-bedroom Toronto apartment, perfect for group trips of up to four guests, is situated in an unspecified area of the city; further details regarding proximity to specific Toronto landmarks such as the CN Tower or the Royal Ontario Museum are needed.
The 1-bathroom flat features a fully equipped kitchen including a fridge, freezer, and dishwasher, air conditioning, parking, and internet access; additional information on the property's size, interior design, and nearby activities is required for a complete description.

Best Oakville vacation rentals with parking

Royal Stays Townhome Collection - 3 Bedroom Townhome In Oakville - Oakville
8.8 17 reviews
Oakville
01/09 – 30/09
$269/nighttotal: $7801 (29 )

Royal Stays Townhome Collection - 3 Bedroom Townhome In Oakville

3 1
apartment , Milton
This 3-bedroom townhouse is located in Oakville, just 27 kilometres from Mississauga Convention Centre and Toronto Pearson International Airport, and 37 kilometres from BMO Field and Budweiser Stage. The property enjoys excellent location and cleanliness ratings, with guests consistently praising its comfort and convenience.
The townhouse offers 172 square metres of space, comfortably accommodating up to 6 guests. A fully equipped kitchen, private terrace, air conditioning, free Wi-Fi, satellite TV, and parking are all provided for your enjoyment.
Furnished 3000 Sqft 4 Bedrooms Home In Oakville - Oakville
10 16 reviews
Oakville
01/08 – 31/10
$237/nighttotal: $21567 (91 )

Furnished 3000 Sqft 4 Bedrooms Home In Oakville

1 3
house , Milton
This spacious townhome is conveniently located in Milton, close to local amenities and attractions. The property has consistently received excellent ratings for cleanliness, location and user experience.
The three-bedroom townhouse comfortably accommodates up to eight guests. It features modern design, a fully equipped kitchen, a private garden, parking, air conditioning, and internet access, making it ideal for families or groups.
Brand New Stylish 2br Condo In Oakville - Oakville
Oakville
01/09 – 28/02
$170/nighttotal: $30600 (180 )

Brand New Stylish 2br Condo In Oakville

2 4
apartment , Milton
This apartment is situated in North Oak, Oakville, a short distance from Sixteen Mile Creek, Lake Ontario, and over 300 kilometres of nature trails, offering convenient access to major highways and Sheridan College.
This stylish 67 square metre flat provides accommodation for up to 4 guests with 2 bedrooms, 2 bathrooms, a fully equipped kitchen including a dishwasher, air conditioning, Wi-Fi, and one complimentary underground parking space, plus in-suite laundry facilities.
Welcome To Your Comfort Retreat By The Lake - Oakville
10 1 review
Oakville
10/07 – 15/07
$1074/nighttotal: $5370 (5 )

Welcome To Your Comfort Retreat By The Lake

4 2
apartment , Toronto
This Burlington residence, located approximately 40 kilometres from the Mississauga Convention Centre and 45 kilometres from Toronto's BMO Field and Budweiser Stage, offers convenient access to the lakefront.
This spacious 300 square metre flat accommodates up to 15 guests, featuring four bathrooms, air conditioning, a well-equipped kitchen, complimentary Wi-Fi, and private parking, with a private swimming pool available for use.

Frequently Asked Questions about vacation rentals in Oakville

  • What should a first-time visitor not miss in Oakville?

    Oakville has a lot to offer, but for a first-timer, you shouldn't miss the waterfront. Stroll along the Oakville Harbour, visit the Oakville Museum, and maybe catch a show at the Oakville Centre for the Performing Arts.
  • What are the best Airbnb and vacation rentals in Oakville?

    Waterfront Coach House Loft, The Wine Cellar and Cozy 2 Bedroom Basement Apartment are the most popular Airbnb and vacation rentals in Oakville among travelers.

  • Which neighborhood in Oakville should you consider for a vacation rental?

    For a vacation rental, you might want to consider the Old Oakville neighbourhood. It's charming, with historic buildings and a vibrant atmosphere, and it's close to the waterfront and shops.
  • What are the most popular Airbnbs in Oakville?

    Among the Airbnbs in Oakville, Waterfront Coach House Loft, The Wine Cellar and Cozy 2 Bedroom Basement Apartment are the most popular ones.

  • What are the top family-friendly attractions in Oakville?

    For families, the Oakville Museum is a great place to start. Kids will love the hands-on exhibits, and the museum's location on the waterfront makes it even more appealing. Also, the Oakville Public Library is a great place to visit with children, with a variety of programs and events.
  • What are the best vacation rentals with a pool in Oakville?

  • When is the best time to book a vacation rental in Oakville?

    The best time to book a vacation rental in Oakville depends on your preferences. If you want to experience the summer festivals and outdoor activities, July and August are ideal. However, for a quieter getaway, spring or autumn might be better.
  • What are the best rentals for families and kids in Oakville?

    The best rentals for families and kids in Oakville are Home Away From Home (Basement Apartment), Pathway Suites and Cozy & Beautiful Basement Apartment.

  • What events or festivals should visitors check out in and around Oakville?

    Oakville has a lively events calendar throughout the year. The Oakville Jazz Festival in July is a popular event, and the Oakville Fall Fair in September is a great family-friendly event. You could also check out the Bronte Creek Provincial Park for events.
  • What are the best rentals or Airbnbs with a jacuzzi in Oakville?

    The best vacation rentals or Airbnb with a jacuzzi in Oakville are Pathway Suites, Beautiful Cozy 1 Br Condo Steps To Sq1 and Luxurious1 Br Condo In Downtown Mississauga .

  • What are the best budget-friendly activities in Oakville?

    Oakville has plenty of free and budget-friendly activities. A walk along the waterfront is always enjoyable, and you can explore the many parks and green spaces. You can also visit the Oakville Public Library, which offers free events and programs.
  • What are the best restaurants with local dishes in Oakville?

    For local dishes, try the Oakville Fish Market for fresh seafood, or The Oakville Chop House for a classic Canadian steakhouse experience. For something a bit more casual, The Oakville Brewing Company serves up delicious pub fare.
  • What are the best walking or cycling routes in Oakville?

    The Waterfront Trail is a popular choice for walking and cycling, offering scenic views of Lake Ontario. The Oakville Creek Trail is another great option, winding through the town's natural areas. You can also check out the trails at Bronte Creek Provincial Park.
  • Are there pet-friendly attractions in Oakville?

    Many parks and green spaces in Oakville are pet-friendly, including the Oakville Harbour. You can also find dog-friendly patios at some restaurants and cafes.
  • What are the benefits of choosing a vacation rental in Oakville?

    Vacation rentals offer more space and privacy compared to hotels. They often come with amenities like kitchens and laundry facilities, which can be convenient for families or longer stays. They can also be a more affordable option, especially for larger groups.
  • What are the top sports attractions and facilities in Oakville?

    Oakville has several sports facilities, including the Oakville Soccer Club, the Oakville Tennis Club, and the Oakville Golf Club. The town also hosts a variety of sporting events throughout the year.

Destinations nearby

Best Oakville vacation rentals with a balcony

Luxury Modern Retreat With Sauna & Modern Amenities - Oakville
Oakville
01/07 – 31/07
$965/nighttotal: $28950 (30 )

Luxury Modern Retreat With Sauna & Modern Amenities

4 4
house , Toronto
This Mississauga property, situated 19 kilometres from Toronto Pearson International Airport and 18 kilometres from the Mississauga Convention Centre, offers convenient access to major attractions.
The 250 square metre modern home boasts four bedrooms, four bathrooms, sleeps nineteen guests, and includes a fully equipped kitchen, sauna, garden, terrace, parking, and Wi-Fi.
3bed Bright Oakville Townhome With Balcony, Office - Oakville
9.0 2 reviews
Oakville
10/07 – 15/07
$379/nighttotal: $1895 (5 )

3bed Bright Oakville Townhome With Balcony, Office

3 2
house , Toronto
This Oakville townhouse is located 26 kilometres from Toronto Pearson International Airport, providing a suburban base with reasonable access to Toronto's attractions.
This property offers free Wi-Fi, private parking, a fully equipped kitchen, and a private balcony, accommodating up to 11 guests with 2 bathrooms and air conditioning.
Luxury 4br Oakville Townhome + 3 Free Parking - Oakville
Oakville
01/09 – 28/02
$208/nighttotal: $37440 (180 )

Luxury 4br Oakville Townhome + 3 Free Parking

4 4
apartment , Hamilton
This spacious four-bedroom townhouse is located in Oakville, a short drive from Downtown Oakville's boutiques, dining, and the Lakeshore, with Glen Abbey Golf Course and the Oakville Museum also nearby.
This 176 square meter property accommodates up to eight guests, featuring four bathrooms, a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a private balcony, and parking for three vehicles.
2 Bedroom Private Suite-parking-near Hospital And Airport - Oakville
9.2 23 reviews
Oakville
31/07 – 31/08
$254/nighttotal: $7874 (31 )

2 Bedroom Private Suite-parking-near Hospital And Airport

2 1
apartment , Milton
This Oakville apartment, situated 22.5km from the Mississauga Convention Centre and 37km from both BMO Field and the Budweiser Stage, offers a peaceful retreat near Milton.
The 19-square-metre, two-bedroom flat sleeps seven, boasting a fully equipped kitchen, terrace, garden, parking, and free Wi-Fi.

Best Oakville vacation rentals with air conditioning

Luxury Executive Studio In Prestigious Glen Abbey Oakville - Oakville
Oakville
01/08 – 30/09
$174/nighttotal: $10440 (60 )

Luxury Executive Studio In Prestigious Glen Abbey Oakville

1 4
studio , Toronto
This one-bedroom apartment is located in the prestigious Glen Abbey community of Oakville, approximately 40 kilometres southwest of Toronto and within easy reach of Bronte Creek Provincial Park.
The 93 square metre studio flat offers a comfortable stay for up to four guests and features a fully equipped kitchen, a king-sized bed, a 55-inch television, and a private patio, perfect for relaxing after a day exploring the surrounding area.
Luxury New Condo In Oakville W/free Parking & Wifi - Oakville
9.7 14 reviews
Oakville
01/07 – 05/07
$250/nighttotal: $1000 (4 )

Luxury New Condo In Oakville W/free Parking & Wifi

1 3
apartment , Hamilton
This two-bedroom, two-bathroom apartment in Hamilton offers convenient access to three major plazas, situated approximately 6.4 kilometres from Costco, The Brick, and Best Buy.
The self-catering flat provides free underground parking, high-speed Wi-Fi, in-suite laundry, a gym, and dining area within the building, comfortably accommodating up to three guests.
Spacious And Luxurious 2br Suite With Huge Windows - Oakville
9.9 16 reviews
Oakville
01/07 – 31/07
$302/nighttotal: $9060 (30 )

Spacious And Luxurious 2br Suite With Huge Windows

1 4
apartment , Toronto
This centrally located Toronto apartment is steps away from numerous shops and restaurants, offering convenient access to the city's attractions.
The two-bedroom flat sleeps five, boasting a full kitchen, laundry facilities, parking, and air conditioning; making it ideal for families or groups visiting Toronto.
Welcome To Your Comfort Retreat By The Lake - Oakville
Oakville
10/07 – 15/07
$1174/nighttotal: $5870 (5 )

Welcome To Your Comfort Retreat By The Lake

4 2
apartment , Toronto
This spacious four-bedroom flat is located in the Bronte neighbourhood of Oakville, placing it 100 metres from the lakeshore and within easy reach of Bronte Harbour and Bronte Heritage Park.
This 307 square metre residence offers accommodation for up to eight guests, featuring a microwave oven, dishwasher, and air conditioning, with parking available and the Joseph Brant Museum and Glen Abbey Golf Course a short drive away for day trips.
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